Office Hours With Spencer Rascoff

We revisit our conversation with Eric Holder. Eric knows a thing or two about introspection. In his current role, companies tap the former U.S. Attorney General to ask difficult questions and help businesses improve everything from diversity to how they work with foreign governments. With the democratization of information and the rise of social media, today's leaders and companies can no longer hide behind a great PR team. According to Holder, "Companies can always be introspective in the same way that we can be as individuals and ask tough questions of ourselves or as corporate entities. What are our strengths? What are our weaknesses? How can we do better?"

It’s no wonder Fortune Magazine called Cindy a “tireless force of nature.” She’s the entrepreneur behind the first-ever FDA approved drug to treat decreased libido in women, and she’s built two businesses from the ground up, selling them for over $1.5 billion. After securing FDA approval for ADDYI, dubbed “female Viagra” by numerous media outlets, Cindy founded The Pink Ceiling, an incubator and venture capital firm dedicated to helping women-focused businesses. In this episode, she and Spencer discuss the importance of empathy in product design, how the #MeToo movement will alter the venture capital landscape and why Cindy is an unapologetic proponent of the color pink.

Arianna Huffington needs little introduction. The author of 15 books, including best-sellers Thrive and The Sleep Revolution, Arianna has been named to Time Magazine’s list of 100 Most Influential People and Forbes’ Most Powerful Women list. In 2016, she stepped down from her namesake Huffington Post (now HuffPost) to launch Thrive Global, which aims to eliminate the stress and burnout that leave so many of us in survival mode. Arianna also joined Uber as its first woman board member, advocating for a culture where “brilliant jerks” aren’t tolerated. In this episode, Arianna joins Spencer at Zillow Group’s New York City office to discuss her newest venture, why leaders need to model balance for their employees and why we all need to prioritize downtime.

Sukhinder is a serial entrepreneur and longtime technology executive who had stints at both Google and Amazon. In 2015, she founded theBoardlist, a talent marketplace for leaders to find highly qualified women to join their boards. Among startups, 57 percent have no women in executive positions. On boards, more than three-quarters of privately funded tech companies have no women, and the picture is even worse among public companies. In this episode, Sukhinder discusses why the tech community should add more women partners, executives and board seats – and why she’s optimistic about the future of women in tech.

Companies that transform our lives with one innovation (like Microsoft Windows) often find it difficult to repeat the same feat because everything - from product to revenue to culture - is built on top of that one big idea. This is the challenge Satya Nadella faced when he took over the reins at Microsoft. How could he ensure that the 43-year-old company seized new opportunities and warded off potential threats? The answer: Build the ability to hit refresh into the culture by focusing on mission, leadership and growth mindset.

Eric Holder knows a thing or two about introspection. In his current role, companies tap the former U.S. Attorney General to ask difficult questions and help businesses improve everything from diversity to how they work with foreign governments. With the democratization of information and the rise of social media, today's leaders and companies can no longer hide behind a great PR team. According to Holder, "Companies can always be introspective in the same way that we can be as individuals and ask tough questions of ourselves or as corporate entities. What are our strengths? What are our weaknesses? How can we do better?"

The companies within Bill Gurley's investment portfolio have some clear similarities: great user-generated content, a reliance on the network effect and a "power to the people" mentality, meaning they put consumers first. But companies don't succeed solely because of their business model or mission - they also need strong leadership. According to Bill, great leaders tend to be unafraid, innately curious and bold. He looks for these qualities in the founder pitching the investment opportunity because - while the idea is important - it's the person who is going to execute it. In this episode, Bill references his 2012 essay, "The Dangerous Seduction of the Lifetime Value (LTV) Formula." You can read it in its entirety here.  

As a founding member of several successful companies (Fog Creek, Trello) in the software development space, you could say that Joel Spolsky knows a bit about developers. On his popular online forum, Stack Overflow, developers ask more than 8,000 questions a day to a community of roughly 40 million developers who visit the site every month. Joel talks about software developers with a reverence normally reserved for philosophers: "Every day, developers get a chance to make a decision that's going to impact the world," he says. But with that power comes great responsibility, and managers have an important role to play in helping developers consider unintended consequences and use their power for good.

When John MacFarlane and his co-founders started Sonos in 2002, they knew nothing about audio or hardware. They simply had an inspiring mission: Fill every home with music. And they knew that the future of music wasn't CDs - it was wireless, digital and connected. In order to stay competitive in an industry that's changing, you have to lead with disruption and never stop improving, and it's this commitment to continuous improvement that has propelled Sonos to outsell some of the world's biggest tech companies in the home audio category.

Comedy writer and producer Robert Carlock's spectacular career includes writing and producing credits on iconic shows such as "Saturday Night Live," "Friends" and "30 Rock." Most recently he co-created the Netflix original series "Unbreakable Kimmy Schmidt," now entering its third season. As a leader in a creative field, Robert doesn't rely on data to make decisions. Instead, he draws largely from his intuition and simply knowing what's going to be funny. And untethering creativity is a lesson all companies and industries can learn from.

Dubbed Silicon Valley's "oddest couple" by The New York Times, together Sheryl Sandberg and Mark Zuckerberg have driven Facebook's astronomical growth and supported one another along the way. The keys to their successful COO-CEO partnership: open communication, commitment to their relationship and shared values.

With a storied career that includes leading coalition forces and counterinsurgency efforts in Iraq and Afghanistan, Retired Army Gen. David Petraeus definitely knows a thing or two about leadership. According to Petraeus, effective leaders don't dictate the tactics; they establish the mission, boundaries and direction, then empower the team to determine the best route. Great leaders also understand that, sometimes, big ideas need to evolve — whether they're running a military operation or private-sector company.

Alaska Airlines CEO Brad Tilden is in the midst of his "what's next" agenda following the company's successful acquisition of Virgin America. Acquisitions, no matter how well executed, are almost always tough on companies. But the commonalities between Alaska and Virgin - their focus on customers and building alignment among employees - lays the foundation for the former competitors to work together and adopt the best features of both airlines as they move forward under a single brand.

With managing a relocation, a mammoth real estate development and significant leadership changes on the coaching staff, L.A. Rams COO Kevin Demoff has a had a tumultuous couple of years. So how does he measure his organization's success? It's all about confidence in the coaching leadership - from the players, the front office and the fans.

Gaming is big business - a fact that perhaps no one knows better than Brandon Beck, co-founder and CEO of Riot Games. Riot's League of Legends is an eSports juggernaut and ushered in a new era of competitive gaming where events draw tens of thousands of spectators and hundreds of thousands more via streaming. Riot hires exclusively gamers, something Brandon admits can be a pain point, but a policy that's essential in understanding League's audience and creating a product that will keep players entertained and challenged over the long term.

Nearly a year and a half ago, The Huffington Post's legendary founder Arianna Huffington recruited Jared Grusd from his role as head of strategy at Spotify to lead Huff Post as she transitioned to her newest business venture. Jared spent an entire year with Arianna learning the ins and outs of her vision for Huff Post and unpacking its core identity and the key drivers of its success. Jared's role, as he put it, was to "figure out the next chapter."    

During her 27 years in the private sector, Secretary Penny Pritzker started five companies, led dozens of businesses and served on the boards of big corporations like Hyatt Hotels, LaSalle National Bank and the William Wrigley Company. When she answered President Obama's call to serve her country, Pritzker's arena switched from private to public, but her objectives and challenges as a leader didn't change.

About this episode's guest: CEO of OpenTable, which was founded nearly 20 years ago Previously CFO of Playdom, which was acquired by Disney in 2010 Left "armchair quarterbacking" on Wall Street for the gaming industry Topics covered in this episode: Broadening the scope of possibilities through technology Balancing a simultaneously mature and entrepreneurial environment Being an innovator in a traditional industry  

About this episode's guest: Founded Box at age 20 with three friends from high school. Prolific user of social media, with 678,000+ followers. Known for wearing bright-colored sneakers. Topics covered in this episode: Why Levie chooses to be outspoken politically. How the future of work is changing. Which types of companies will and won't be disrupted -- and why. The benefits of being a publicly traded company. Differences between the San Francisco and Seattle tech and venture capital scenes.    

With her longstanding Wall Street career (Citigroup, Merrill Lynch) and unique perspective as a woman in a predominantly male industry, Sallie Krawcheck is tackling a question that has mystified investment banks for decades: how to successfully market wealth management services to women. As CEO of digital financial investment platform Ellevest, she sees diversity as the greatest advantage in cracking the code. Krawcheck encourages each employee to bring their "whole self" to work, and emphasizes hiring the best fit for the team, which in some cases could be a different choice than the person who traditionally would be considered the best fit for the role.